Sulfanilamidopyrimidine-formaldehyde condensation products



and V @Nns@n The two new compounds are obtained by re- Patented Jan. 16 1951 UNITED STATES PATENT ()FFICE SULFANILAMIDOPYRIMIDINE-FORMALDE- HYDE CONDENSATION PRODUCTS Jean Druey, Riehen, Switzerland, assignor to Ciba Pharmaceutical Products, Inc., Summit, N. J.

No Drawing. Application December 19, 1949, Se-

rial No. 133,941. In Switzerland December 19,

1 Claim. (01. 26 023 9.75)

This application is a continuation-in-part of my copending application Serial Number 784,518, filed November 6, 1947.

The present invention relates to therapeutically useful sulfanilamidopyrimidine formaldehyde condensation products of the formulae CHzO CzHs CHzO C2115 acting 2-sulfanilamido-pyrimidine with formaldehyde and ethanol or propanol, respectively. The compounds are crystallized and their properties are superior to those of the sulfanilamido- Example 1 parts by weight of 2-sulfanilamidopyrimidine are suspended in 350 parts by volume of ethyl alcohol, the suspension heated to C. while stirring, and then admixed with a warm mixture of 22.5 parts by volume of 40% aqueous formaldehyde solution and parts by volume of 50% ethyl alcohol. A further 22.5 parts by volume of 40% aqueous formaldehyde solution are then gradually added While stirring, a clear solution being formed. Upon cooling, the condensation product precipitates in fine form. There are obtained 28 parts by weight of a nearly white powder which is soluble in dilute caustic soda solution and which melts at about 192 C.

with decomposition. The compound corresponds to the formula NHS Q K Example 2 parts by weight of sulfanilamidopyrimidine are suspended in a mixture of 1400 parts by volume of propanol and 1400 parts by volume of CHzO C2115 CHzOCzHs water, and heated to the boil. 450 parts by volume of a 40% aqueous solution of formaldehyde, diluted with 500 parts by volume of water are added, a clear solution being formed. Upon cooling and standing, the reaction product precipitates in the form ofcolorless needles. After about 24 hours they are separated by suction-filtering and dried at 60 C. The yield is parts by weight. Analysis shows that the new compound corresponds to the formula It melts at 151-153 C.

Having thus described the invention, what is claimed is:

A sulfanilamidopyrimidine formaldehyde condensation product of the group consisting of the compounds of the formulae CHzO C3111 JEAN DRUEY.

No references cited. 

